JPWO2017038968A1 - Compound purification method - Google Patents
Compound purification method Download PDFInfo
- Publication number
- JPWO2017038968A1 JPWO2017038968A1 JP2017538124A JP2017538124A JPWO2017038968A1 JP WO2017038968 A1 JPWO2017038968 A1 JP WO2017038968A1 JP 2017538124 A JP2017538124 A JP 2017538124A JP 2017538124 A JP2017538124 A JP 2017538124A JP WO2017038968 A1 JPWO2017038968 A1 JP WO2017038968A1
- Authority
- JP
- Japan
- Prior art keywords
- group
- integer
- carbon atoms
- purifying
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000003883 substance clean up Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 54
- 238000000034 method Methods 0.000 claims abstract description 52
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 39
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 22
- 125000003118 aryl group Chemical group 0.000 claims abstract description 22
- 239000002904 solvent Substances 0.000 claims abstract description 21
- 125000006165 cyclic alkyl group Chemical group 0.000 claims abstract description 14
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000001424 substituent group Chemical group 0.000 claims abstract description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- 239000004305 biphenyl Chemical group 0.000 claims abstract description 7
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 7
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 239000012528 membrane Substances 0.000 claims description 22
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 18
- 239000011148 porous material Substances 0.000 claims description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000011651 chromium Substances 0.000 claims description 10
- 239000012510 hollow fiber Substances 0.000 claims description 10
- 229920002647 polyamide Polymers 0.000 claims description 9
- 239000004952 Polyamide Substances 0.000 claims description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 8
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 7
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 6
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 claims description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 5
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052804 chromium Inorganic materials 0.000 claims description 5
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 claims description 5
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 4
- 229920005672 polyolefin resin Polymers 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000000243 solution Substances 0.000 description 62
- 229910052751 metal Inorganic materials 0.000 description 28
- 239000002184 metal Substances 0.000 description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 238000000746 purification Methods 0.000 description 17
- -1 trimethylnonyl alcohol Chemical compound 0.000 description 16
- 238000005259 measurement Methods 0.000 description 13
- 239000007788 liquid Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- 229910001873 dinitrogen Inorganic materials 0.000 description 10
- 239000004698 Polyethylene Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- 238000001914 filtration Methods 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000004677 Nylon Substances 0.000 description 5
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 5
- 229920001778 nylon Polymers 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000004065 semiconductor Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229920001971 elastomer Polymers 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920006122 polyamide resin Polymers 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- 229920006169 Perfluoroelastomer Polymers 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- GJRQTCIYDGXPES-UHFFFAOYSA-N isobutyl acetate Chemical compound CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropyl acetate Chemical compound CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- OENHRRVNRZBNNS-UHFFFAOYSA-N naphthalene-1,8-diol Chemical compound C1=CC(O)=C2C(O)=CC=CC2=C1 OENHRRVNRZBNNS-UHFFFAOYSA-N 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- GJQIMXVRFNLMTB-UHFFFAOYSA-N nonyl acetate Chemical compound CCCCCCCCCOC(C)=O GJQIMXVRFNLMTB-UHFFFAOYSA-N 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical compound CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 description 1
- ZWPUOFSQNASCII-UHFFFAOYSA-N 1-(2-ethoxyethoxy)butane Chemical compound CCCCOCCOCC ZWPUOFSQNASCII-UHFFFAOYSA-N 0.000 description 1
- BIJNHUAPTJVVNQ-UHFFFAOYSA-N 1-Hydroxypyrene Chemical compound C1=C2C(O)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 BIJNHUAPTJVVNQ-UHFFFAOYSA-N 0.000 description 1
- MQGIBEAIDUOVOH-UHFFFAOYSA-N 1-[2-[2-[2-(2-butoxyethoxy)ethoxy]ethoxy]ethoxy]butane Chemical compound CCCCOCCOCCOCCOCCOCCCC MQGIBEAIDUOVOH-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 1
- BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical compound CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 description 1
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- AWBIJARKDOFDAN-UHFFFAOYSA-N 2,5-dimethyl-1,4-dioxane Chemical compound CC1COC(C)CO1 AWBIJARKDOFDAN-UHFFFAOYSA-N 0.000 description 1
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 1
- GZMAAYIALGURDQ-UHFFFAOYSA-N 2-(2-hexoxyethoxy)ethanol Chemical compound CCCCCCOCCOCCO GZMAAYIALGURDQ-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- BJINVQNEBGOMCR-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl acetate Chemical compound COCCOCCOC(C)=O BJINVQNEBGOMCR-UHFFFAOYSA-N 0.000 description 1
- CUDYYMUUJHLCGZ-UHFFFAOYSA-N 2-(2-methoxypropoxy)propan-1-ol Chemical compound COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 description 1
- HQLKZWRSOHTERR-UHFFFAOYSA-N 2-Ethylbutyl acetate Chemical compound CCC(CC)COC(C)=O HQLKZWRSOHTERR-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- WFSMVVDJSNMRAR-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethanol Chemical compound CCOCCOCCOCCO WFSMVVDJSNMRAR-UHFFFAOYSA-N 0.000 description 1
- SDHQGBWMLCBNSM-UHFFFAOYSA-N 2-[2-(2-methoxyethoxy)ethoxy]ethyl acetate Chemical compound COCCOCCOCCOC(C)=O SDHQGBWMLCBNSM-UHFFFAOYSA-N 0.000 description 1
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 description 1
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 description 1
- WOYWLLHHWAMFCB-UHFFFAOYSA-N 2-ethylhexyl acetate Chemical compound CCCCC(CC)COC(C)=O WOYWLLHHWAMFCB-UHFFFAOYSA-N 0.000 description 1
- CETWDUZRCINIHU-UHFFFAOYSA-N 2-heptanol Chemical compound CCCCCC(C)O CETWDUZRCINIHU-UHFFFAOYSA-N 0.000 description 1
- PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-methyl-1-pentanol Chemical compound CCCC(C)CO PFNHSEQQEPMLNI-UHFFFAOYSA-N 0.000 description 1
- CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 description 1
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- BRRVXFOKWJKTGG-UHFFFAOYSA-N 3,3,5-trimethylcyclohexanol Chemical compound CC1CC(O)CC(C)(C)C1 BRRVXFOKWJKTGG-UHFFFAOYSA-N 0.000 description 1
- PKNKULBDCRZSBT-UHFFFAOYSA-N 3,4,5-trimethylnonan-2-one Chemical compound CCCCC(C)C(C)C(C)C(C)=O PKNKULBDCRZSBT-UHFFFAOYSA-N 0.000 description 1
- YHCCCMIWRBJYHG-UHFFFAOYSA-N 3-(2-ethylhexoxymethyl)heptane Chemical compound CCCCC(CC)COCC(CC)CCCC YHCCCMIWRBJYHG-UHFFFAOYSA-N 0.000 description 1
- JSGVZVOGOQILFM-UHFFFAOYSA-N 3-methoxy-1-butanol Chemical compound COC(C)CCO JSGVZVOGOQILFM-UHFFFAOYSA-N 0.000 description 1
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical compound COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 1
- LDMRLRNXHLPZJN-UHFFFAOYSA-N 3-propoxypropan-1-ol Chemical compound CCCOCCCO LDMRLRNXHLPZJN-UHFFFAOYSA-N 0.000 description 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 1
- LBKMJZAKWQTTHC-UHFFFAOYSA-N 4-methyldioxolane Chemical compound CC1COOC1 LBKMJZAKWQTTHC-UHFFFAOYSA-N 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- PCFMUWBCZZUMRX-UHFFFAOYSA-N 9,10-Dihydroxyanthracene Chemical compound C1=CC=C2C(O)=C(C=CC=C3)C3=C(O)C2=C1 PCFMUWBCZZUMRX-UHFFFAOYSA-N 0.000 description 1
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 description 1
- AQKOPTQQYRJSSF-UHFFFAOYSA-N C(CCCCC)OCCO.C(CCC)OCCO Chemical compound C(CCCCC)OCCO.C(CCC)OCCO AQKOPTQQYRJSSF-UHFFFAOYSA-N 0.000 description 1
- YYLLIJHXUHJATK-UHFFFAOYSA-N Cyclohexyl acetate Chemical compound CC(=O)OC1CCCCC1 YYLLIJHXUHJATK-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- HXQPUEQDBSPXTE-UHFFFAOYSA-N Diisobutylcarbinol Chemical compound CC(C)CC(O)CC(C)C HXQPUEQDBSPXTE-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- RZKSECIXORKHQS-UHFFFAOYSA-N Heptan-3-ol Chemical compound CCCCC(O)CC RZKSECIXORKHQS-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- JKRZOJADNVOXPM-UHFFFAOYSA-N Oxalic acid dibutyl ester Chemical compound CCCCOC(=O)C(=O)OCCCC JKRZOJADNVOXPM-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- LTOATULEBMBWSO-UHFFFAOYSA-N acetic acid;2-ethoxyethanol Chemical compound CC(O)=O.CCOCCO LTOATULEBMBWSO-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- HUFIRBOBXZUFPV-UHFFFAOYSA-N benzene-1,3-diol Chemical compound OC1=CC=CC(O)=C1.OC1=CC=CC(O)=C1 HUFIRBOBXZUFPV-UHFFFAOYSA-N 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- BTMVHUNTONAYDX-UHFFFAOYSA-N butyl propionate Chemical compound CCCCOC(=O)CC BTMVHUNTONAYDX-UHFFFAOYSA-N 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 238000010981 drying operation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- UHKJHMOIRYZSTH-UHFFFAOYSA-N ethyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OCC UHKJHMOIRYZSTH-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 1
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 1
- RXTNIJMLAQNTEG-UHFFFAOYSA-N hexan-2-yl acetate Chemical compound CCCCC(C)OC(C)=O RXTNIJMLAQNTEG-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- IMXBRVLCKXGWSS-UHFFFAOYSA-N methyl 2-cyclohexylacetate Chemical compound COC(=O)CC1CCCCC1 IMXBRVLCKXGWSS-UHFFFAOYSA-N 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- 229940054192 micro-guard Drugs 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229940017144 n-butyl lactate Drugs 0.000 description 1
- QJQAMHYHNCADNR-UHFFFAOYSA-N n-methylpropanamide Chemical compound CCC(=O)NC QJQAMHYHNCADNR-UHFFFAOYSA-N 0.000 description 1
- XOOMNEFVDUTJPP-UHFFFAOYSA-N naphthalene-1,3-diol Chemical compound C1=CC=CC2=CC(O)=CC(O)=C21 XOOMNEFVDUTJPP-UHFFFAOYSA-N 0.000 description 1
- PCILLCXFKWDRMK-UHFFFAOYSA-N naphthalene-1,4-diol Chemical compound C1=CC=C2C(O)=CC=C(O)C2=C1 PCILLCXFKWDRMK-UHFFFAOYSA-N 0.000 description 1
- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 0.000 description 1
- ZUVBIBLYOCVYJU-UHFFFAOYSA-N naphthalene-1,7-diol Chemical compound C1=CC=C(O)C2=CC(O)=CC=C21 ZUVBIBLYOCVYJU-UHFFFAOYSA-N 0.000 description 1
- JRNGUTKWMSBIBF-UHFFFAOYSA-N naphthalene-2,3-diol Chemical compound C1=CC=C2C=C(O)C(O)=CC2=C1 JRNGUTKWMSBIBF-UHFFFAOYSA-N 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 1
- GXOHBWLPQHTYPF-UHFFFAOYSA-N pentyl 2-hydroxypropanoate Chemical compound CCCCCOC(=O)C(C)O GXOHBWLPQHTYPF-UHFFFAOYSA-N 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- BRGJIIMZXMWMCC-UHFFFAOYSA-N tetradecan-2-ol Chemical compound CCCCCCCCCCCCC(C)O BRGJIIMZXMWMCC-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XMUJIPOFTAHSOK-UHFFFAOYSA-N undecan-2-ol Chemical compound CCCCCCCCCC(C)O XMUJIPOFTAHSOK-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D63/00—Apparatus in general for separation processes using semi-permeable membranes
- B01D63/02—Hollow fibre modules
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D63/00—Apparatus in general for separation processes using semi-permeable membranes
- B01D63/14—Pleat-type membrane modules
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/26—Polyalkenes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/26—Polyalkenes
- B01D71/261—Polyethylene
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/30—Polyalkenyl halides
- B01D71/32—Polyalkenyl halides containing fluorine atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/56—Polyamides, e.g. polyester-amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/14—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with at least one hydroxy group on a condensed ring system containing two rings
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
Abstract
本発明に係る化合物の精製方法は、下記式(A0)及び/又は(B0)で表されるヒドロキシ置換芳香族化合物及び溶媒を含む溶液を、フィルターに通液する工程を含む。【化1】(前記式(A0)中、n0は0〜9の整数であり、m0は0〜2の整数であり、p0は0〜9の整数であり、ここで、m0が1のとき、前記式(A0)はナフタレン骨格又はビフェニル骨格を有することを示し、Raは各々独立して、水酸基、ハロゲン基、炭素数1〜40の直鎖状、分岐状若しくは環状のアルキル基、置換基を有していてもよい炭素数6〜40のアリール基、又は炭素数2〜40のアルケニル基及びそれらの組み合わせからなる群より選択される基であり、該アルキル基、該アリール基又は該アルケニル基は、エーテル結合、ケトン結合、あるいはエステル結合を含んでいてもよい。前記式(B0)中、n1は0〜9の整数であり、p1は0〜9の整数であり、Rbは各々独立して、水素原子、水酸基、ハロゲン基、炭素数1〜40の直鎖状、分岐状若しくは環状のアルキル基、置換基を有していてもよい炭素数6〜40のアリール基、又は炭素数2〜40のアルケニル基及びそれらの組み合わせからなる群より選択される基であり、該アルキル基、該アリール基又は該アルケニル基は、エーテル結合、ケトン結合、あるいはエステル結合を含んでいてもよい。)The method for purifying a compound according to the present invention includes a step of passing a solution containing a hydroxy-substituted aromatic compound represented by the following formula (A0) and / or (B0) and a solvent through a filter. (In the formula (A0), n0 is an integer of 0 to 9, m0 is an integer of 0 to 2, and p0 is an integer of 0 to 9, where m0 is 1. The formula (A0) indicates that it has a naphthalene skeleton or a biphenyl skeleton, and each Ra independently represents a hydroxyl group, a halogen group, a linear, branched or cyclic alkyl group having 1 to 40 carbon atoms, a substituent. A group selected from the group consisting of an aryl group having 6 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms and a combination thereof, which may have an alkyl group, an aryl group or an alkenyl group The group may contain an ether bond, a ketone bond, or an ester bond, In the formula (B0), n1 is an integer of 0 to 9, p1 is an integer of 0 to 9, and Rb is independent from each other. A hydrogen atom, a hydroxyl group, a halogen group, From a linear, branched or cyclic alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 40 carbon atoms which may have a substituent, or an alkenyl group having 2 to 40 carbon atoms and combinations thereof And the alkyl group, the aryl group or the alkenyl group may contain an ether bond, a ketone bond, or an ester bond.)
Description
本発明は、化合物(例えば、ヒドロキシ置換芳香族化合物)の精製方法に関する。 The present invention relates to a method for purifying a compound (for example, a hydroxy-substituted aromatic compound).
ジヒドロキシナフタレン等のヒドロキシ置換芳香族化合物は、半導体用の封止材、コーティング剤、レジスト用材料、半導体下層膜形成材料として使用される化合物又は樹脂の原料として有用である(例えば、特許文献1〜2参照)。また、ジヒドロキシナフタレン等のヒドロキシ置換芳香族化合物の精製方法として、特定の方法が知られている(例えば、特許文献3参照)。 Hydroxy-substituted aromatic compounds such as dihydroxynaphthalene are useful as a raw material for compounds or resins used as semiconductor sealing materials, coating agents, resist materials, semiconductor underlayer film forming materials (for example, Patent Documents 1 to 3). 2). Moreover, a specific method is known as a purification method of hydroxy-substituted aromatic compounds such as dihydroxynaphthalene (see, for example, Patent Document 3).
上記用途においては、特に金属含有量が、歩留まり向上のために重要な性能評価項目となっている。すなわち、ヒドロキシ置換芳香族化合物を原料として得られる化合物又は樹脂中に金属が多く含まれる場合には、半導体中に金属が残存し、半導体の電気特性を低下させることから、不純物としての金属含有量を低減することが求められている。
ヒドロキシ置換芳香族化合物から得られる化合物又は樹脂の金属含有量を低減するための精製方法として、該化合物又は樹脂と有機溶媒を含む混合物にイオン交換水又は純水を加えることで再結晶を行った後、固液分離を行う方法、該化合物又は樹脂を水と任意に混和しない有機溶媒に溶解させ、その溶液を水溶液と接触させ抽出処理を行うことにより、金属分を水相に移行させたのち、有機相と水相を分液して金属含有量を低減させる方法が考えられる。
しかしながら、上記方法では、金属含有量の高いヒドロキシ置換芳香族化合物を原料として用いると、特定の金属種に対する除去効果が十分ではないという問題がある。
したがって、金属含有量の低減された高純度のヒドロキシ置換芳香族化合物の工業的に有利な精製方法の確立が望まれている。
また、ヒドロキシ置換芳香族化合物の純度が低い場合、当該ヒドロキシ置換芳香族化合物から得られる化合物又は樹脂の収率が下がる、もしくはばらつくという問題がある。
さらに、従来、開示されている精製方法では、金属含有量を低減することについて検討されておらず、金属含有量の低減が不十分である。
本発明の目的は、ヒドロキシ置換芳香族化合物を工業的に有利に精製するための方法を提供することにある。In the above applications, particularly the metal content is an important performance evaluation item for improving the yield. In other words, when a metal or a compound obtained using a hydroxy-substituted aromatic compound as a raw material contains a large amount of metal, the metal remains in the semiconductor and deteriorates the electrical characteristics of the semiconductor. There is a need to reduce the above.
As a purification method for reducing the metal content of a compound or resin obtained from a hydroxy-substituted aromatic compound, recrystallization was performed by adding ion-exchanged water or pure water to a mixture containing the compound or resin and an organic solvent. Thereafter, a method of performing solid-liquid separation, the compound or resin is dissolved in an organic solvent which is not arbitrarily miscible with water, and the solution is brought into contact with an aqueous solution to perform extraction treatment, thereby transferring the metal component to the aqueous phase. A method of reducing the metal content by separating the organic phase and the aqueous phase is conceivable.
However, in the above method, when a hydroxy-substituted aromatic compound having a high metal content is used as a raw material, there is a problem that the effect of removing specific metal species is not sufficient.
Therefore, establishment of an industrially advantageous purification method for a high-purity hydroxy-substituted aromatic compound with a reduced metal content is desired.
Moreover, when the purity of a hydroxy substituted aromatic compound is low, there exists a problem that the yield of the compound or resin obtained from the said hydroxy substituted aromatic compound falls or varies.
Further, conventionally, the disclosed purification methods have not been studied on reducing the metal content, and the reduction of the metal content is insufficient.
An object of the present invention is to provide a method for industrially advantageously purifying hydroxy-substituted aromatic compounds.
本発明者らは上記課題を解決するため鋭意検討した結果、ヒドロキシ置換芳香族化合物と溶媒を含む溶液をフィルターに通液させることにより、当該溶液中の金属分の含有量が顕著に低減されることを見出し、本発明に至った。
すなわち、本発明は次のとおりである。
[1]
下記式(A0)及び/又は(B0)で表されるヒドロキシ置換芳香族化合物及び溶媒を含む溶液を、フィルターに通液する工程を含む、化合物の精製方法。
[2]
前記ヒドロキシ置換芳香族化合物が、下記式(A)及び/又は(B)で表される化合物である、[1]に記載の化合物の精製方法。
[3]
前記ヒドロキシ置換芳香族化合物が、下記式(A−1)で表される化合物、下記式(A−2)で表される化合物、下記式(A−3)で表される化合物、下記式(A−4)で表される化合物、及び下記式(B−1)で表される化合物からなる群より選ばれる1種以上である、[1]に記載の化合物の精製方法。
[4]
前記ヒドロキシ置換芳香族化合物が、下記式(1)で表される化合物である、[1]に記載の化合物の精製方法。
前記ヒドロキシ置換芳香族化合物が、2,6−ジヒドロキシナフタレン及び2,7−ジヒドロキシナフタレンからなる群より選ばれる1種以上である、[1]に記載の化合物の精製方法。
[6]
前記フィルターの公称孔径が1.0μm未満である、[1]〜[5]のいずれかに記載の化合物の精製方法。
[7]
前記フィルターが、中空糸膜フィルター、メンブレンフィルター及びプリーツ膜フィルターからなる群より選ばれる1種以上である、[1]〜[6]のいずれかに記載の化合物の精製方法。
[8]
前記フィルターの濾材が、ポリアミド製、ポレオレフィン樹脂製及びフッ素樹脂製からなる群より選ばれる1種以上である、[1]〜[7]のいずれかに記載の化合物の精製方法。
[9]
前記フィルターが、イオン交換体を含む、[1]〜[8]のいずれかに記載の化合物の精製方法。
[10]
前記フィルターが、ゼータ電位を有する物質を含む、[1]〜[9]のいずれかに記載の化合物の精製方法。
[11]
前記溶媒が、酢酸エチル、酢酸ブチル、メチルイソブチルケトン、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、シクロペンタノン及びシクロヘキサノンからなる群より選ばれる1種以上である、[1]〜[10]のいずれかに記載の化合物の精製方法。
[12]
前記溶液の調製及び通液が、酸素濃度が20%未満の雰囲気で行われる、[1]〜[11]のいずれかに記載の化合物の精製方法。
[13]
前記溶液中に含まれるクロムの含有量が、前記ヒドロキシ置換芳香族化合物の質量に対して50ppb以下に低減される、[1]〜[12]のいずれかに記載の化合物の精製方法。As a result of intensive studies to solve the above problems, the inventors of the present invention significantly reduce the metal content in the solution by passing a solution containing the hydroxy-substituted aromatic compound and the solvent through the filter. As a result, they have reached the present invention.
That is, the present invention is as follows.
[1]
A method for purifying a compound, comprising a step of passing a solution containing a hydroxy-substituted aromatic compound represented by the following formula (A 0 ) and / or (B 0 ) and a solvent through a filter.
[2]
The method for purifying a compound according to [1], wherein the hydroxy-substituted aromatic compound is a compound represented by the following formula (A) and / or (B).
[3]
The hydroxy-substituted aromatic compound is a compound represented by the following formula (A-1), a compound represented by the following formula (A-2), a compound represented by the following formula (A-3), the following formula ( The method for purifying a compound according to [1], which is at least one selected from the group consisting of a compound represented by A-4) and a compound represented by the following formula (B-1).
[4]
The method for purifying a compound according to [1], wherein the hydroxy-substituted aromatic compound is a compound represented by the following formula (1).
The method for purifying a compound according to [1], wherein the hydroxy-substituted aromatic compound is at least one selected from the group consisting of 2,6-dihydroxynaphthalene and 2,7-dihydroxynaphthalene.
[6]
The method for purifying a compound according to any one of [1] to [5], wherein the filter has a nominal pore size of less than 1.0 μm.
[7]
The method for purifying a compound according to any one of [1] to [6], wherein the filter is one or more selected from the group consisting of a hollow fiber membrane filter, a membrane filter, and a pleated membrane filter.
[8]
The method for purifying a compound according to any one of [1] to [7], wherein the filter medium of the filter is at least one selected from the group consisting of polyamide, polyolefin resin, and fluororesin.
[9]
The method for purifying a compound according to any one of [1] to [8], wherein the filter contains an ion exchanger.
[10]
The method for purifying a compound according to any one of [1] to [9], wherein the filter contains a substance having a zeta potential.
[11]
[1] to [10], wherein the solvent is at least one selected from the group consisting of ethyl acetate, butyl acetate, methyl isobutyl ketone, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, cyclopentanone and cyclohexanone. A method for purifying the compound according to any one of the above.
[12]
The method for purifying a compound according to any one of [1] to [11], wherein the solution is prepared and passed in an atmosphere having an oxygen concentration of less than 20%.
[13]
The method for purifying a compound according to any one of [1] to [12], wherein a content of chromium contained in the solution is reduced to 50 ppb or less with respect to a mass of the hydroxy-substituted aromatic compound.
本発明により、ヒドロキシ置換芳香族化合物を工業的に有利に精製することができる。 According to the present invention, a hydroxy-substituted aromatic compound can be purified industrially advantageously.
以下、本発明の実施形態(以下「本実施形態」とも記す。)について詳細に説明する。なお、以下の実施形態は、本発明を説明するための例示であり、本発明はその実施形態のみに限定されない。 Hereinafter, embodiments of the present invention (hereinafter also referred to as “present embodiments”) will be described in detail. In addition, the following embodiment is an illustration for demonstrating this invention, and this invention is not limited only to the embodiment.
本実施形態に係る化合物の精製方法は、下記式(A0)及び/又は(B0)で表されるヒドロキシ置換芳香族化合物及び溶媒を含む溶液を、フィルターに通液する工程を含む。上記のように構成されているため、本実施形態に係る化合物の精製方法により、ヒドロキシ置換芳香族化合物を工業的に有利に精製することができる。特に、後述する実施例に示すとおり、ジヒドロキシナフタレン溶液中に含まれるクロム(Cr)の含有量については、当該ジヒドロキシナフタレンの質量に対して50ppb以下にまで低減することが可能である。
上記のとおり、本実施形態における「精製」とは、ヒドロキシ置換芳香族化合物と共存し得る金属成分を十分に低減する操作を意味し、具体的には、Na量が50ppb以下、Fe量が60ppb以下、Cr量が70ppb以下、及びSn量が50ppb以下であるヒドロキシ置換芳香族化合物が得られる。本実施形態においては、精製後のヒドロキシ置換芳香族化合物と共存し得るNa量が50ppb以下、Fe量が50ppb以下、Cr量が50ppb以下、及びSn量が50ppb以下であることが好ましい。これらの金属成分量は後述する実施例に記載の方法で測定することができる。
なお、本実施形態における「通液」とは、上記溶液がフィルターの外部から当該フィルターの内部を通過して再度フィルターの外部へと移動することを意味し、例えば、上記溶液を単にフィルターの表面で接触させる態様や、上記溶液を当該表面上で接触させつつイオン交換樹脂の外部で移動させる態様(すなわち、単に接触する態様)は除外される。The method for purifying a compound according to this embodiment includes a step of passing a solution containing a hydroxy-substituted aromatic compound represented by the following formula (A 0 ) and / or (B 0 ) and a solvent through a filter. Since it is configured as described above, the hydroxy-substituted aromatic compound can be industrially advantageously purified by the compound purification method according to this embodiment. In particular, as shown in the examples described later, the content of chromium (Cr) contained in the dihydroxynaphthalene solution can be reduced to 50 ppb or less with respect to the mass of the dihydroxynaphthalene.
As described above, “purification” in the present embodiment means an operation for sufficiently reducing the metal component that can coexist with the hydroxy-substituted aromatic compound. Specifically, the amount of Na is 50 ppb or less and the amount of Fe is 60 ppb. Thereafter, a hydroxy-substituted aromatic compound having a Cr amount of 70 ppb or less and a Sn amount of 50 ppb or less is obtained. In this embodiment, it is preferable that the amount of Na that can coexist with the hydroxy-substituted aromatic compound after purification is 50 ppb or less, the amount of Fe is 50 ppb or less, the amount of Cr is 50 ppb or less, and the amount of Sn is 50 ppb or less. These metal component amounts can be measured by the method described in Examples described later.
In the present embodiment, “liquid passage” means that the solution passes from the outside of the filter to the inside of the filter and moves again to the outside of the filter. For example, the solution is simply passed through the surface of the filter. And a mode in which the solution is moved outside the ion exchange resin while being in contact with the surface (that is, a mode of simply contacting) are excluded.
本実施形態に係る化合物の精製方法において、原料の供給性の観点から、前記ヒドロキシ置換芳香族化合物は、下記式(A)及び/又は(B)で表される化合物であることがより好ましい。 In the method for purifying a compound according to this embodiment, the hydroxy-substituted aromatic compound is more preferably a compound represented by the following formula (A) and / or (B) from the viewpoint of feedability of raw materials.
本実施形態に係る化合物の精製方法において、有機溶媒に対する溶解性の観点から、前記ヒドロキシ置換芳香族化合物は、下記式(A−1)で表される化合物、下記式(A−2)で表される化合物、下記式(A−3)で表される化合物、下記式(A−4)で表される化合物、及び下記式(B−1)で表される化合物からなる群より選ばれる1種以上であることがさらに好ましい。 In the method for purifying a compound according to this embodiment, from the viewpoint of solubility in an organic solvent, the hydroxy-substituted aromatic compound is a compound represented by the following formula (A-1), represented by the following formula (A-2). 1 selected from the group consisting of a compound represented by the following formula (A-3), a compound represented by the following formula (A-4), and a compound represented by the following formula (B-1) More preferably, it is a seed or more.
本実施形態に係る化合物の精製方法において、有機溶媒に対する溶解性および精製の釜効率の観点から、前記ヒドロキシ置換芳香族化合物は、下記式(1)で表される化合物であることが特に好ましい。
ここで、上記式(1)で表される化合物は、特に限定されないが、原料の供給性の観点から、1,2−ジヒドロキシナフタレン、1,3−ジヒドロキシナフタレン、1,4−ジヒドロキシナフタレン、1,5−ジヒドロキシナフタレン、1,6−ジヒドロキシナフタレン、1,7−ジヒドロキシナフタレン、1,8−ジヒドロキシナフタレン、2,3−ジヒドロキシナフタレン、2,6−ジヒドロキシナフタレン及び2,7−ジヒドロキシナフタレンからなる群より選ばれる1種以上が好ましい。 Here, the compound represented by the above formula (1) is not particularly limited, but 1,2-dihydroxynaphthalene, 1,3-dihydroxynaphthalene, 1,4-dihydroxynaphthalene, 1, , 5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 1,8-dihydroxynaphthalene, 2,3-dihydroxynaphthalene, 2,6-dihydroxynaphthalene and 2,7-dihydroxynaphthalene One or more selected from the above are preferred.
また、上記式(1)で表される化合物は、特に限定されないが、式(1)で表される化合物を原料として得られる化合物又は樹脂の耐熱性の観点から、2,6−ジヒドロキシナフタレン及び2,7−ジヒドロキシナフタレンからなる群より選ばれる1種以上がより好ましい。 Further, the compound represented by the formula (1) is not particularly limited, but 2,6-dihydroxynaphthalene and a compound obtained from the compound represented by the formula (1) or a resin obtained from the viewpoint of heat resistance. One or more selected from the group consisting of 2,7-dihydroxynaphthalene is more preferable.
上記式(1)で表される化合物は、特に限定されないが、式(1)で表される化合物を原料として得られる化合物又は樹脂のさらなる耐熱性の観点から、2,6−ジヒドロキシナフタレンがさらに好ましい。 The compound represented by the above formula (1) is not particularly limited, but 2,6-dihydroxynaphthalene is further added from the viewpoint of further heat resistance of the compound or resin obtained using the compound represented by the formula (1) as a raw material. preferable.
本実施形態で使用されるヒドロキシ置換芳香族化合物は、製造メーカー及び試薬メーカー等公知の手段にて容易に入手できる。また、公知の手法を応用して適宜合成することができ、その合成手法は特に限定されない。 The hydroxy-substituted aromatic compound used in the present embodiment can be easily obtained by known means such as a manufacturer and a reagent manufacturer. Moreover, it can synthesize | combine suitably applying a well-known method, The synthesis | combining method is not specifically limited.
本実施形態で使用するヒドロキシ置換芳香族化合物は単独でもよいが、2種以上混合することもできる。また、ヒドロキシ置換芳香族化合物は、各種界面活性剤、各種架橋剤、各種酸発生剤、各種安定剤等を含有したものであってもよい。 Although the hydroxy substituted aromatic compound used by this embodiment may be individual, 2 or more types can also be mixed. Further, the hydroxy-substituted aromatic compound may contain various surfactants, various crosslinking agents, various acid generators, various stabilizers and the like.
本実施形態で使用される溶媒としては、特に限定されないが、半導体製造プロセスに安全に適用できる有機溶媒が好ましい。使用する溶媒の量は、使用する式(1)で表される化合物に対して、通常1〜100質量倍が溶解性の向上と精製後の固体回収の容易さの観点から好ましい。より好ましくは5〜50質量倍、さらに好ましくは10〜50質量倍である。 The solvent used in the present embodiment is not particularly limited, but an organic solvent that can be safely applied to a semiconductor manufacturing process is preferable. The amount of the solvent to be used is preferably 1 to 100 times by mass with respect to the compound represented by the formula (1) to be used, from the viewpoint of improved solubility and ease of solid recovery after purification. More preferably, it is 5-50 mass times, More preferably, it is 10-50 mass times.
本実施形態で使用される溶媒の具体例としては、以下に限定されないが、エチルエーテル、イソプロピルエーテル、n−ブチルエーテル、ヘキシルエーテル、2−エチルヘキシルエーテル、エチレンオキシド、1,2−プロピレンオキシド、ジオキソラン、4−メチルジオキソラン、ジオキサン、ジメチルジオキサン、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールジエチルエーテル、エチレングリコールモノブチルエーテルエチレングリコールモノ−n−ヘキシルエーテル、エチレングリコールモノフェニルエーテル、エチレングリコールモノ−2−エチルブチルエーテル、エチレングリコールジブチルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールジエチルエーテル、ジエチレングリコールモノブチルエーテル、ジエチレングリコールジブチルエーテル、ジエチレングリコールモノ−n−ヘキシルエーテル、エトキシトリグリコール、テトラエチレングリコールジブチルエーテル、プロピレングリコールモノメチルエーテル(PGME)、ジプロピレングリコールメチルエーテル、トリプロピレングリコールメチルエーテル、プロピレングリコールモノプロピルエーテル、テトラヒドロフラン、2−メチルテトラヒドロフランなどのエーテル類、メタノール、エタノール、n−プロパノール、i−プロパノール、n−ブタノール、i−ブタノール、sec−ブタノール、t−ブタノール、n−ペンタノール、i−ペンタノール、2−メチルブタノール、sec−ペンタノール、t−ペンタノール、3−メトキシブタノール、n−ヘキサノール、2−メチルペンタノール、sec−ヘキサノール、2−エチルブタノール、sec−ヘプタノール、ヘプタノール−3、n−オクタノール、2−エチルヘキサノール、sec−オクタノール、ノニルアルコール、2,6−ジメチル−4−ヘプタノール、n−デカノール、sec−ウンデシルアルコール、トリメチルノニルアルコール、sec−テトラデシルアルコール、sec−ヘプタデシルアルコール、フェノール、シクロヘキサノール、メチルシクロヘキサノール、3,3,5−トリメチルシクロヘキサノール、ベンジルアルコール、フェニルメチルカルビノール、ジアセトンアルコール、クレゾールなどのモノアルコール類、ジエチルカーボネート、酢酸メチル、酢酸エチル、γ−ブチロラクトン、γ−バレロラクトン、酢酸n−プロピル、酢酸i−プロピル、酢酸n−ブチル、酢酸i−ブチル、酢酸sec−ブチル、酢酸n−ペンチル、酢酸sec−ペンチル、酢酸3−メトキシブチル、酢酸メチルペンチル、酢酸2−エチルブチル、酢酸2−エチルヘキシル、酢酸ベンジル、酢酸シクロヘキシル、酢酸メチルシクロヘキシル、酢酸ノニル、アセト酢酸メチル、アセト酢酸エチル、酢酸エチレングリコールモノメチルエーテル、酢酸エチレングリコールモノエチルエーテル、酢酸プロピレングリコールモノメチルエーテル、酢酸ジエチレングリコールモノメチルエーテル、酢酸ジエチレングリコールモノエチルエーテル、酢酸ジエチレングリコールモノブチルエーテル、ジ酢酸グリコール、酢酸メトキシトリグリコール、プロピオン酸エチル、プロピオン酸n−ブチル、プロピオン酸i−ペンチル、メトキシプロピオン酸メチル、エトキシプロピオン酸エチル、シュウ酸ジエチル、シュウ酸ジ−n−ブチル、乳酸メチル、乳酸エチル、乳酸n−ブチル、乳酸n−ペンチル、マロン酸ジエチル、フタル酸ジメチル、フタル酸ジエチル等のエステル類、アセトン、メチルエチルケトン、メチル−n−プロピルケトン、メチル−n−ブチルケトン、ジエチルケトン、メチルイソブチルケトン、メチル−n−ペンチルケトン、エチルブチルケトン、メチルヘキシルケトン、ジイソブチルケトン、トリメチルノナノン、シクロヘキサノン、メチルシクロヘキサノン、2,4−ペンタンジオン、アセトニルアセトン、アセトフェノン、N−メチルピロリドン等のケトン類、エチレングリコールモノエチルエーテルアセテート、エチレングリコールモノブチルエーテルアセテート、プロピレングリコールモノメチルエーテルアセテート(PGMEA)、プロピレングリコールモノエチルエーテルアセテート等のグリコールエーテルアセテート類、N−メチルホルムアミド、N,N−ジメチルホルムアミド、N,N−ジエチルホルムアミド、アセトアミド、N−メチルアセトアミド、N,N−ジメチルアセトアミド、N−メチルプロピオンアミド、N−メチルピロリドンなどの窒素化合物系溶媒、n−ヘキサン、n−ヘプタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類、塩化メチレン、クロロホルム等のハロゲン化炭化水素類等が挙げられる。
上記溶媒はそれぞれ単独で用いることもできるし、また2種以上を混合して用いることもできる。
上述した中でも、作業性や仕込み量の管理のし易さの観点から、酢酸エチル、酢酸ブチル、メチルイソブチルケトン、プロピレングリコールモノメチルエーテル(PGME)、プロピレングリコールモノメチルエーテルアセテート(PGMEA)、シクロペンタノン及びシクロヘキサノンからなる群より選ばれる1種以上であることが好ましい。Specific examples of the solvent used in the present embodiment are not limited to the following, but include ethyl ether, isopropyl ether, n-butyl ether, hexyl ether, 2-ethylhexyl ether, ethylene oxide, 1,2-propylene oxide, dioxolane, 4 -Methyldioxolane, dioxane, dimethyldioxane, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol diethyl ether, ethylene glycol monobutyl ether ethylene glycol mono-n-hexyl ether, ethylene glycol monophenyl ether, ethylene glycol mono-2- Ethyl butyl ether, ethylene glycol dibutyl ether, diethylene glycol monomethyl ether, diethylene glycol Noethyl ether, diethylene glycol diethyl ether, diethylene glycol monobutyl ether, diethylene glycol dibutyl ether, diethylene glycol mono-n-hexyl ether, ethoxytriglycol, tetraethylene glycol dibutyl ether, propylene glycol monomethyl ether (PGME), dipropylene glycol methyl ether, tripropylene Glycol methyl ether, propylene glycol monopropyl ether, ethers such as tetrahydrofuran and 2-methyltetrahydrofuran, methanol, ethanol, n-propanol, i-propanol, n-butanol, i-butanol, sec-butanol, t-butanol, n -Pentanol, i-pentanol, 2-methylbuta , Sec-pentanol, t-pentanol, 3-methoxybutanol, n-hexanol, 2-methylpentanol, sec-hexanol, 2-ethylbutanol, sec-heptanol, heptanol-3, n-octanol, 2 -Ethylhexanol, sec-octanol, nonyl alcohol, 2,6-dimethyl-4-heptanol, n-decanol, sec-undecyl alcohol, trimethylnonyl alcohol, sec-tetradecyl alcohol, sec-heptadecyl alcohol, phenol, cyclo Monoalcohols such as hexanol, methylcyclohexanol, 3,3,5-trimethylcyclohexanol, benzyl alcohol, phenylmethyl carbinol, diacetone alcohol, cresol, diethyl carbonate -Bonate, methyl acetate, ethyl acetate, γ-butyrolactone, γ-valerolactone, n-propyl acetate, i-propyl acetate, n-butyl acetate, i-butyl acetate, sec-butyl acetate, n-pentyl acetate, sec-acetate Pentyl, 3-methoxybutyl acetate, methylpentyl acetate, 2-ethylbutyl acetate, 2-ethylhexyl acetate, benzyl acetate, cyclohexyl acetate, methyl cyclohexyl acetate, nonyl acetate, methyl acetoacetate, ethyl acetoacetate, ethylene glycol monomethyl ether, acetic acid Ethylene glycol monoethyl ether, propylene glycol monomethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, diacetic acid Glycol, methoxytriglycol acetate, ethyl propionate, n-butyl propionate, i-pentyl propionate, methyl methoxypropionate, ethyl ethoxypropionate, diethyl oxalate, di-n-butyl oxalate, methyl lactate, ethyl lactate , Esters such as n-butyl lactate, n-pentyl lactate, diethyl malonate, dimethyl phthalate, diethyl phthalate, acetone, methyl ethyl ketone, methyl n-propyl ketone, methyl n-butyl ketone, diethyl ketone, methyl isobutyl ketone , Methyl-n-pentyl ketone, ethyl butyl ketone, methyl hexyl ketone, diisobutyl ketone, trimethylnonanone, cyclohexanone, methylcyclohexanone, 2,4-pentanedione, acetonyl acetone, acetopheno , Ketones such as N-methylpyrrolidone, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate (PGMEA), glycol ether acetates such as propylene glycol monoethyl ether acetate, N-methylformamide, N, N-dimethylformamide, N, N-diethylformamide, acetamide, N-methylacetamide, N, N-dimethylacetamide, N-methylpropionamide, N-methylpyrrolidone and other nitrogen compound solvents, n-hexane, n -Aliphatic hydrocarbons such as heptane, aromatic hydrocarbons such as toluene and xylene, and halogenated hydrocarbons such as methylene chloride and chloroform.
The above solvents can be used alone or in combination of two or more.
Among the above, from the viewpoint of workability and ease of management of the charged amount, ethyl acetate, butyl acetate, methyl isobutyl ketone, propylene glycol monomethyl ether (PGME), propylene glycol monomethyl ether acetate (PGMEA), cyclopentanone and It is preferably at least one selected from the group consisting of cyclohexanone.
本実施形態における通液の際、ヒドロキシ置換芳香族化合物と溶媒を含む溶液中の金属分の除去に用いられるフィルターは、通常、液体ろ過用として市販されているものを使用することができる。フィルターの濾過精度は特に限定されないが、フィルターの公称孔径は1.0μm未満であることが好ましく、0.2μm以下であることがより好ましく、0.05μm以下であることがさらに好ましい。また、フィルターの公称孔径の下限値は、特に限定されないが、通常、0.005μmである。ここでいう公称孔径とは、フィルターの分離性能を示す名目上の孔径であり、例えば、バブルポイント試験、水銀圧入法試験、標準粒子補足試験など、フィルターの製造元により決められた試験法により決定される孔径である。市販品を用いた場合、製造元のカタログデータに記載の値である。公称孔径を1.0μm未満にすることで、ヒドロキシ置換芳香族化合物の溶液を1回フィルターに通液させた後の金属分の含有量をより効果的に低減できる傾向にある。特に、クロム(Cr)の含有量をヒドロキシ置換芳香族化合物の質量に対して、好ましくは50ppb以下、より好ましくは20ppb以下、さらに好ましくは5ppb以下に低減することができる傾向にある。本実施形態においては、ヒドロキシ置換芳香族化合物の溶液の各金属分の含有量をより低減させるために、通液を2回以上行ってもよい。 In passing through the liquid in the present embodiment, a filter that is usually used for liquid filtration can be used as a filter used for removing a metal component in a solution containing a hydroxy-substituted aromatic compound and a solvent. The filtration accuracy of the filter is not particularly limited, but the nominal pore size of the filter is preferably less than 1.0 μm, more preferably 0.2 μm or less, and even more preferably 0.05 μm or less. The lower limit value of the nominal pore diameter of the filter is not particularly limited, but is usually 0.005 μm. The nominal pore diameter here is a nominal pore diameter indicating the separation performance of the filter, and is determined by a test method determined by the filter manufacturer, such as a bubble point test, a mercury intrusion test, a standard particle supplement test, etc. The hole diameter. When a commercial product is used, the value is described in the catalog data of the manufacturer. By setting the nominal pore diameter to less than 1.0 μm, the content of the metal after the solution of the hydroxy-substituted aromatic compound is passed through the filter once tends to be more effectively reduced. In particular, the chromium (Cr) content tends to be preferably 50 ppb or less, more preferably 20 ppb or less, and even more preferably 5 ppb or less with respect to the mass of the hydroxy-substituted aromatic compound. In this embodiment, in order to further reduce the content of each metal component in the solution of the hydroxy-substituted aromatic compound, the liquid may be passed twice or more.
フィルターの形態としては、以下に限定されないが、例えば、中空糸膜フィルター、メンブレンフィルター、プリーツ膜フィルター、並びに不織布、セルロース、及びケイソウ土などの濾材を充填したフィルターなどを用いることができる。特に高精細な濾過精度と他の形態と比較した濾過面積の高さから、フィルターは、中空糸膜フィルター、メンブレンフィルター及びプリーツ膜フィルターからなる群より選ばれる1種以上であることが好ましく、中空糸膜フィルターを用いることがより好ましい。 The form of the filter is not limited to the following. For example, a hollow fiber membrane filter, a membrane filter, a pleated membrane filter, and a filter filled with a filter medium such as nonwoven fabric, cellulose, and diatomaceous earth can be used. The filter is preferably at least one selected from the group consisting of a hollow fiber membrane filter, a membrane filter, and a pleated membrane filter, particularly because of the high-definition filtration accuracy and the height of the filtration area compared with other forms. It is more preferable to use a thread membrane filter.
上記フィルターの材質は、以下に限定されないが、例えば、ポリエチレン、ポリプロピレン等のポリオレフィン樹脂製、ポリアミド樹脂製、ポリエステル、ポリアクリロニトリルなどの極性基含有樹脂製、フッ化ポリエチレン(PTFE)などのフッ素含有樹脂製を挙げることができる。本実施形態において、耐熱性と耐溶媒性の観点から、フィルターの濾材が、ポリアミド樹脂製、ポレオレフィン樹脂製及びフッ素樹脂製からなる群より選ばれる1種以上であることが好ましく、より好ましくはポリアミド樹脂製である。
ポリアミド系フィルターとしては(以下、商標)、以下に限定されないが、例えば、キッツマイクロフィルター(株)製のポリフィックスナイロンシリーズ、日本ポール(株)製のウルチプリーツP−ナイロン66、ウルチポアN66、スリーエム(株)製のライフアシュアPSNシリーズ、ライフアシュアEFシリーズなどを挙げることができる。
ポリオレフィン系フィルターとしては、以下に限定されないが、例えば、日本ポール(株)製のウルチプリーツPEクリーン、日本インテグリス(株)製のマイクロガードプラスHC10、オプチマイザーD等を挙げることができる。
フッ素樹脂系フィルターとしては、以下に限定されないが、例えば、日本ポール(株)製のエンフロンHTPFR、スリーエム(株)製のライフシュアFAシリーズ等を挙げることができる。
これらのフィルターはそれぞれ単独で用いても2種類以上を組み合わせて用いてもよい。The material of the filter is not limited to the following, but, for example, a polyolefin resin such as polyethylene or polypropylene, a polyamide resin, a polar group-containing resin such as polyester or polyacrylonitrile, or a fluorine-containing resin such as fluorinated polyethylene (PTFE) Can be mentioned. In the present embodiment, from the viewpoint of heat resistance and solvent resistance, the filter medium is preferably at least one selected from the group consisting of polyamide resin, polyolefin resin, and fluororesin, more preferably. Made of polyamide resin.
Examples of the polyamide-based filter (hereinafter referred to as “trademark”) include, but are not limited to, for example, Polyfix nylon series manufactured by KITZ Micro Filter Co., Ltd., ULTI PLEAT P-Nylon 66 manufactured by Nihon Pall Co., Ltd., ULTIMORE N66, 3M Examples include Life Assure PSN series and Life Assure EF series manufactured by KK.
Examples of the polyolefin filter include, but are not limited to, Ultiplez PE Clean manufactured by Nippon Pole Co., Ltd., Microguard Plus HC10 manufactured by Nihon Integris Co., Ltd., and Optimizer D.
Examples of the fluororesin filter include, but are not limited to, Enflon HTPFR manufactured by Nippon Pole Co., Ltd., Lifesure FA series manufactured by 3M Co., Ltd., and the like.
These filters may be used alone or in combination of two or more.
また、上記フィルターには陽イオン交換樹脂などのイオン交換体や、濾過される有機溶媒溶液にゼータ電位を生じさせるカチオン電荷調節剤などが含まれていてもよい。例えば、ポリアミドポリアミンエピクロロヒドリンカチオン樹脂などの正のゼータ電位を有する物質を含むフィルターとして(以下、商標)、以下に限定されないが、例えば、スリーエム(株)製ゼータプラス40QSHやゼータプラス020GN、あるいはライフアシュアEFシリーズ等が挙げられる。 In addition, the filter may contain an ion exchanger such as a cation exchange resin, a cation charge control agent that generates a zeta potential in the organic solvent solution to be filtered, and the like. For example, as a filter containing a substance having a positive zeta potential such as a polyamide polyamine epichlorohydrin cation resin (hereinafter referred to as a trademark), but not limited to the following, for example, Zeta Plus 40QSH or Zeta Plus 020GN manufactured by 3M Corporation, Or Life Assure EF series etc. are mentioned.
特にクロム(Cr)やスズ(Sn)などの重金属を効果的に低減させるフィルターの材質として、ポリアミド樹脂が好ましい理由としては、金属の吸着性能に優れることが挙げられる。フィルター材質の金属の吸着性能については、フィルターと同じ材質のシート(以下「基材」と称する。)と前記ヒドロキシ置換化合物を溶解させた溶液との接触角を測定し、該金属の低減挙動を比較することにより、確認することができる。具体的には、基材との接触角が小さいほど、溶液とフィルター表面との濡れ性が高くなり、接触角の大きな基材に比べ、フィルターのろ過精度が同一であっても、該金属をさらに低減することが可能となる。 In particular, as a material for a filter that effectively reduces heavy metals such as chromium (Cr) and tin (Sn), a polyamide resin is preferable because of its excellent metal adsorption performance. Regarding the metal adsorption performance of the filter material, the contact angle between a sheet of the same material as the filter (hereinafter referred to as “base material”) and a solution in which the hydroxy-substituted compound is dissolved is measured, and the reduction behavior of the metal is measured. This can be confirmed by comparison. Specifically, the smaller the contact angle with the substrate, the higher the wettability between the solution and the filter surface, and even if the filtration accuracy of the filter is the same as compared with a substrate with a large contact angle, the metal Further reduction is possible.
本実施形態におけるヒドロキシ置換芳香族化合物及び溶媒を含む溶液と基材との接触角としては、1°〜40°の範囲が好ましく、より好ましくは1°〜30°であり、さらに好ましくは1°〜20°である。接触角が1°〜40°の範囲であると、基材への濡れ性が十分であり、良好な吸着性能が得られる傾向にある。 In the present embodiment, the contact angle between the substrate containing the hydroxy-substituted aromatic compound and the solvent and the substrate is preferably in the range of 1 ° to 40 °, more preferably 1 ° to 30 °, and even more preferably 1 °. ~ 20 °. When the contact angle is in the range of 1 ° to 40 °, the wettability to the substrate is sufficient, and good adsorption performance tends to be obtained.
また、フィルターの接続ジョイント、ハウジングに含まれるO−リング等のパッキング部材の少なくとも一種は、パーフルオロゴム、パーフルオロエラストマーからなり、これらの構成部材全てが、フッ素含有樹脂、パーフルオロゴム、パーフルオロエラストマーから選ばれる材料で構成されていることが好ましい。さらに、上記のパッキング部材は、パーフルオロゴム、パーフルオロエラストマーから選ばれる材料で構成されていることが特に好ましい。これら以外の部材のみでは、ヒドロキシ置換芳香族化合物中の金属化合物の含有率がppbレベルまで低減できない場合がある。 In addition, at least one of packing members such as filter connection joints and O-rings included in the housing is made of perfluoro rubber or perfluoro elastomer, and all of these components are made of fluorine-containing resin, perfluoro rubber, perfluoro. It is preferably made of a material selected from elastomers. Furthermore, the packing member is particularly preferably made of a material selected from perfluoro rubber and perfluoro elastomer. Only with other members, the content of the metal compound in the hydroxy-substituted aromatic compound may not be reduced to the ppb level.
ヒドロキシ置換芳香族化合物の溶液の調製及び通液の際の温度は、高すぎると、溶媒の種類によっては加水分解が生じる傾向にあり、揮発性の酸が遊離する場合があるため好ましくなく、低すぎると、ヒドロキシ置換芳香族化合物の溶解度が小さくなる傾向にある。このように、揮発性の酸の遊離を防止する観点及び効率性の観点から、温度を調整することが好ましく、通常は0〜40℃とすることができ、好ましくは5〜30℃であり、より好ましくは10〜25℃。 If the temperature for preparing and passing the solution of the hydroxy-substituted aromatic compound is too high, hydrolysis tends to occur depending on the type of solvent, and volatile acids may be liberated. When too large, the solubility of the hydroxy-substituted aromatic compound tends to be small. Thus, from the viewpoint of preventing the liberation of volatile acids and from the viewpoint of efficiency, it is preferable to adjust the temperature, usually 0 to 40 ° C, preferably 5 to 30 ° C, More preferably, it is 10-25 degreeC.
なお、本実施形態においては、上述した通液により精製されたヒドロキシ置換芳香族化合物を得る工程以外に、さらなる精製工程を。 In addition, in this embodiment, the further refinement | purification process other than the process of obtaining the hydroxy substituted aromatic compound refine | purified by the liquid flow mentioned above.
こうして得られたヒドロキシ置換芳香族化合物と溶媒を含む溶液に混入する水分は、減圧蒸留等の操作を施すことにより容易に除去できる。また、必要により溶媒を加え、ヒドロキシ置換芳香族化合物の濃度を任意の濃度に調整することができる。 The water mixed in the solution containing the hydroxy-substituted aromatic compound and the solvent thus obtained can be easily removed by performing an operation such as vacuum distillation. Further, if necessary, a solvent can be added to adjust the concentration of the hydroxy-substituted aromatic compound to an arbitrary concentration.
ヒドロキシ置換芳香族化合物と溶媒を含む溶液から、ヒドロキシ置換芳香族化合物のみを得る方法は、特に限定されず、例えば、減圧除去、再沈殿による分離、及びそれらの組み合わせ等、公知の方法で行うことができる。必要に応じて、濃縮操作、ろ過操作、遠心分離操作、乾燥操作等の公知の処理を行うことができる。 The method for obtaining only the hydroxy-substituted aromatic compound from the solution containing the hydroxy-substituted aromatic compound and the solvent is not particularly limited, and may be performed by a known method such as removal under reduced pressure, separation by reprecipitation, or a combination thereof. Can do. If necessary, known processes such as a concentration operation, a filtration operation, a centrifugal separation operation, and a drying operation can be performed.
本実施形態におけるヒドロキシ置換芳香族化合物及び溶媒を含む溶液の調製及び通液は、酸素濃度が20%未満の雰囲気で行われることが好ましい。酸素濃度は10%未満がより好ましく、5%未満がさらに好ましく、1%未満が特に好ましい。酸素濃度を20%未満にすることにより、ヒドロキシ置換芳香族化合物の変質がより抑制される傾向にあり、より高純度のヒドロキシ置換芳香族化合物が得られる傾向にある。 The preparation and flow of the solution containing the hydroxy-substituted aromatic compound and the solvent in this embodiment are preferably performed in an atmosphere having an oxygen concentration of less than 20%. The oxygen concentration is more preferably less than 10%, further preferably less than 5%, and particularly preferably less than 1%. By making the oxygen concentration less than 20%, the alteration of the hydroxy-substituted aromatic compound tends to be further suppressed, and a higher-purity hydroxy-substituted aromatic compound tends to be obtained.
酸素濃度を低下させる方法は、公知の方法で実施でき、特に限定されないが、例えば、精製を行うカラム又は釜に窒素をフローして、あるいは減圧してその後窒素を導入することで、ガス置換を行うことができる。精製を行うカラム又は釜を減圧してその後窒素を導入することが簡便かつ確実で好ましい。 The method for reducing the oxygen concentration can be carried out by a known method, and is not particularly limited. For example, the gas replacement is performed by flowing nitrogen into a column or kettle for purification or by introducing nitrogen after reducing the pressure. It can be carried out. It is convenient, reliable and preferable that the column or kettle for purification is decompressed and then nitrogen is introduced.
酸素濃度の確認は、公知の方法で実施でき、特に限定されないが、例えば、精製を行う釜に窒素をフローして、ベントから排出されるガスの酸素濃度を、酸素濃度計にて測定することができる。また、精製を行う釜に酸素濃度計を設置することもできる。 Confirmation of the oxygen concentration can be carried out by a known method, and is not particularly limited. For example, the oxygen concentration of the gas discharged from the vent is measured with an oximeter by flowing nitrogen into a refining kettle. Can do. An oxygen concentration meter can also be installed in the kettle for purification.
以下、実施例を挙げて、本実施形態をさらに具体的に説明する。但し、本実施形態は、これらの実施例に限定されない。 Hereinafter, the present embodiment will be described more specifically with reference to examples. However, the present embodiment is not limited to these examples.
(実施例1)
クラス1000のクリーンブース内にて、1000mL容量の四つ口フラスコ(底抜き型)に、有機純度99.3%の2,6−ジヒドロキシナフタレン(以下、2,6−DHNとも称する。)をプロピレングリコールモノメチルエーテル(PGME)に溶解させた溶液(濃度2.5質量%)を500g仕込み、続いて釜内部の空気を減圧除去した後、窒素ガスを導入して大気圧まで戻し、窒素ガスを毎分100mLで通気下、内部の酸素濃度を1%未満に調整した後、攪拌しながら30℃まで加熱した。真空ポンプで底抜きバルブ直下からフィルター通液ラインの終点までの空気を減圧除去した後、底抜きバルブから2,6−DHN溶液を抜き出し、フッ素樹脂製の耐圧チューブを経由して、ダイヤフラムポンプで毎分100mLの流量で公称孔径が0.01μmのポリアミド製中空糸膜フィルター(キッツマイクロフィルター(株)製、商品名:ポリフィックスナイロンシリーズ)に通液した。得られた2,6−DHN溶液を下記条件にて分析した。なお、酸素濃度は、アズワン株式会社製の酸素濃度計「OM−25MF10」により測定した(以下も同様とした。)。Example 1
In a Class 1000 clean booth, 2,6-dihydroxynaphthalene (hereinafter, also referred to as 2,6-DHN) with an organic purity of 99.3% is propylene in a 1000 mL four-necked flask (bottomed type). 500 g of a solution (concentration of 2.5% by mass) dissolved in glycol monomethyl ether (PGME) was added, and after the air inside the kettle was removed under reduced pressure, nitrogen gas was introduced and returned to atmospheric pressure. The inside oxygen concentration was adjusted to less than 1% under aeration at 100 mL / min, and then heated to 30 ° C. with stirring. The vacuum pump removes the air from directly under the bottom valve to the end of the filter liquid line under reduced pressure, then withdraws the 2,6-DHN solution from the bottom valve and passes through the fluororesin pressure tube and the diaphragm pump. The solution was passed through a polyamide hollow fiber membrane filter (trade name: Polyfix nylon series, manufactured by KITZ Micro Filter Co., Ltd.) having a nominal pore size of 0.01 μm at a flow rate of 100 mL per minute. The obtained 2,6-DHN solution was analyzed under the following conditions. The oxygen concentration was measured with an oxygen concentration meter “OM-25MF10” manufactured by AS ONE Co., Ltd. (the same applies hereinafter).
(実施例2)
公称孔径が0.01μmのポリエチレン製中空糸膜フィルター(キッツマイクロフィルター(株)製、商品名:ポリフィックス)を使用した以外は、実施例1と同様に通液し、得られた2,6−DHN溶液を下記条件にて分析した。(Example 2)
Except for using a polyethylene hollow fiber membrane filter having a nominal pore size of 0.01 μm (product name: Polyfix, manufactured by KITZ Micro Filter Co., Ltd.), the obtained 2,6 was passed through in the same manner as in Example 1. -The DHN solution was analyzed under the following conditions.
(実施例3)
公称孔径が0.05μmのポリアミド製中空糸膜フィルター(キッツマイクロフィルター(株)製、商品名:ポリフィックス)を使用した以外は、実施例1と同様に通液し、得られた2,6−DHN溶液を下記条件にて分析した。(Example 3)
Except for using a polyamide hollow fiber membrane filter having a nominal pore size of 0.05 μm (trade name: Polyfix, manufactured by KITZ Micro Filter Co., Ltd.), obtained in the same manner as in Example 1, and obtained 2,6 -The DHN solution was analyzed under the following conditions.
(実施例4)
公称孔径が0.05μmのポリエチレン製メンブレンフィルター(日本ポール(株)製、商品名:ウルチプリーツPEクリーン)を使用した以外は、実施例1と同様に通液し、得られた2,6−DHN溶液を下記条件にて分析した。Example 4
The obtained 2,6-liquid was passed through in the same manner as in Example 1 except that a polyethylene membrane filter having a nominal pore size of 0.05 μm (manufactured by Nippon Pole Co., Ltd., trade name: Ultipleat PE Clean) was used. The DHN solution was analyzed under the following conditions.
(実施例5)
公称孔径が0.05μmのPTFE製メンブレンフィルター(Millipore(株)製、商品名:オムニポア)を使用した以外は、実施例1と同様に通液し、得られた2,6−DHN溶液を下記条件にて分析した。(Example 5)
The obtained 2,6-DHN solution was passed through in the same manner as in Example 1 except that a PTFE membrane filter having a nominal pore size of 0.05 μm (trade name: Omnipore manufactured by Millipore) was used. Analysis was performed under conditions.
(実施例6)
公称孔径が0.2μmのゼータプラスフィルター40QSH(スリーエム(株)製、イオン交換能あり)を使用した以外は、実施例1と同様に通液し、得られた2,6−DHN溶液を下記条件にて分析した。(Example 6)
The obtained 2,6-DHN solution was passed through in the same manner as in Example 1 except that a zeta plus filter 40QSH (manufactured by 3M Co., Ltd., with ion exchange capability) having a nominal pore size of 0.2 μm was used. Analysis was performed under conditions.
(実施例7)
公称孔径が0.2μmのゼータプラスフィルター020GN(スリーエム(株)製、イオン交換能あり)を使用した以外は、実施例1と同様に通液し、得られた2,6−DHN溶液を下記条件にて分析した。(Example 7)
The obtained 2,6-DHN solution was passed through in the same manner as in Example 1 except that a zeta plus filter 020GN (manufactured by 3M Co., Ltd., with ion exchange capability) having a nominal pore size of 0.2 μm was used. Analysis was performed under conditions.
(実施例8)窒素ガス置換なし
クラス1000のクリーンブース内にて、1000mL容量の四つ口フラスコ(底抜き型)に、有機純度99.3%の2,6−DHNをPGMEに溶解させた溶液(濃度2.5質量%)を500g仕込み、攪拌しながら30℃まで加熱した。底抜きバルブから2,6−DHN溶液を抜き出し、フッ素樹脂製の耐圧チューブを経由してダイヤフラムポンプで毎分100mLの流量で公称孔径が0.01μmのポリアミド製中空糸膜フィルター(キッツマイクロフィルター(株)製、商品名:ポリフィックスナイロンシリーズ)に通液した。得られた2,6−DHN溶液を下記条件にて分析した。(Example 8) No nitrogen gas replacement In a class 1000 clean booth, 2,6-DHN having an organic purity of 99.3% was dissolved in PGME in a 1000 mL four-necked flask (bottomed mold). 500 g of a solution (concentration: 2.5% by mass) was charged and heated to 30 ° C. with stirring. A 2,6-DHN solution is extracted from the bottom valve, and a hollow fiber membrane filter made of polyamide with a nominal pore size of 0.01 μm at a flow rate of 100 mL / min with a diaphragm pump via a pressure-resistant tube made of fluororesin (KITZ microfilter ( (Trade name: Polyfix nylon series). The obtained 2,6-DHN solution was analyzed under the following conditions.
(実施例9)
クラス1000のクリーンブース内にて、1000mL容量の四つ口フラスコ(底抜き型)に、有機純度99.3%の2,6−DHNをPGMEに溶解させた溶液(濃度2.5質量%)を500g仕込み、続いて釜内部の空気を減圧除去した後、窒素ガスを導入して大気圧まで戻し、窒素ガスを毎分100mLで通気下、内部の酸素濃度1%未満に調整した後、攪拌しながら30℃まで加熱した。底抜きバルブから2,6−DHN溶液を抜き出し、フッ素樹脂製の耐圧チューブを経由してダイヤフラムポンプで毎分100mLの流量で公称孔径が1.0μmのポリエチレン製膜フィルター(日本ポール(株)製、商品名:ウルチブリーツPEクリーン)に通液した。得られた2,6−DHN溶液を下記条件にて分析した。Example 9
In a Class 1000 clean booth, a solution of 2,6-DHN with an organic purity of 99.3% in PGME (concentration 2.5% by mass) in a 1000 mL four-necked flask (bottom mold) Was added, and the air inside the kettle was removed under reduced pressure. Then, nitrogen gas was introduced to return to atmospheric pressure, and the nitrogen gas was aerated at 100 mL / min, and the internal oxygen concentration was adjusted to less than 1%, followed by stirring. While heating to 30 ° C. A 2,6-DHN solution is extracted from the bottom valve, and a polyethylene membrane filter having a nominal pore diameter of 1.0 μm at a flow rate of 100 mL / min with a diaphragm pump via a pressure-resistant tube made of fluororesin (manufactured by Nippon Pole Co., Ltd.) , Trade name: ULBLE BREATH PE CLEAN). The obtained 2,6-DHN solution was analyzed under the following conditions.
(実施例10)
クラス1000のクリーンブース内にて、1000mL容量の四つ口フラスコ(底抜き型)に、有機純度99.3%の2,6−DHNをPGMEに溶解させた溶液(濃度2.5質量%)を500g仕込み、続いて釜内部の空気を減圧除去した後、窒素ガスを導入して大気圧まで戻し、窒素ガスを毎分100mLで通気下、内部の酸素濃度を5.0%に調整した後、攪拌しながら30℃まで加熱した。真空ポンプで底抜きバルブ直下からフィルター通液ラインの終点までの空気を減圧除去した後、底抜きバルブから2,6−DHN溶液を抜き出し、フッ素樹脂製の耐圧チューブを経由して、ダイヤフラムポンプで毎分100mLの流量で公称孔径が0.01μmのポリアミド製中空糸膜フィルター(キッツマイクロフィルター(株)製、商品名:ポリフィックスナイロンシリーズ)に通液した。得られた2,6−DHN溶液を下記条件にて分析した。(Example 10)
In a Class 1000 clean booth, a solution of 2,6-DHN with an organic purity of 99.3% in PGME (concentration 2.5% by mass) in a 1000 mL four-necked flask (bottom mold) After the pressure inside the kettle was removed under reduced pressure, nitrogen gas was introduced and returned to atmospheric pressure, and the nitrogen gas was vented at 100 mL / min and the oxygen concentration inside was adjusted to 5.0%. The mixture was heated to 30 ° C. with stirring. The vacuum pump removes the air from directly under the bottom valve to the end of the filter liquid line under reduced pressure, then withdraws the 2,6-DHN solution from the bottom valve and passes through the fluororesin pressure tube and the diaphragm pump. The solution was passed through a polyamide hollow fiber membrane filter (trade name: Polyfix nylon series, manufactured by KITZ Micro Filter Co., Ltd.) having a nominal pore size of 0.01 μm at a flow rate of 100 mL per minute. The obtained 2,6-DHN solution was analyzed under the following conditions.
(実施例11)
クラス1000のクリーンブース内にて、1000mL容量の四つ口フラスコ(底抜き型)に、有機純度99.3%の2,6−DHNをPGMEに溶解させた溶液(濃度2.5質量%)を500g仕込み、続いて釜内部の空気を減圧除去した後、窒素ガスを導入して大気圧まで戻し、窒素ガスを毎分100mLで通気下、内部の酸素濃度を10.0%に調整した後、攪拌しながら30℃まで加熱した。真空ポンプで底抜きバルブ直下からフィルター通液ラインの終点までの空気を減圧除去した後、底抜きバルブから2,6−DHN溶液を抜き出し、フッ素樹脂製の耐圧チューブを経由して、ダイヤフラムポンプで毎分100mLの流量で公称孔径が0.01μmのポリアミド製中空糸膜フィルター(キッツマイクロフィルター(株)製、商品名:ポリフィックスナイロンシリーズ)に通液した。得られた2,6−DHN溶液を下記条件にて分析した。(Example 11)
In a Class 1000 clean booth, a solution of 2,6-DHN with an organic purity of 99.3% in PGME (concentration 2.5% by mass) in a 1000 mL four-necked flask (bottom mold) After the air inside the kettle was removed under reduced pressure, nitrogen gas was introduced and the pressure was returned to atmospheric pressure. After nitrogen gas was vented at 100 mL / min and the internal oxygen concentration was adjusted to 10.0% The mixture was heated to 30 ° C. with stirring. The vacuum pump removes the air from directly under the bottom valve to the end of the filter liquid line under reduced pressure, then withdraws the 2,6-DHN solution from the bottom valve and passes through the fluororesin pressure tube and the diaphragm pump. The solution was passed through a polyamide hollow fiber membrane filter (trade name: Polyfix nylon series, manufactured by KITZ Micro Filter Co., Ltd.) having a nominal pore size of 0.01 μm at a flow rate of 100 mL per minute. The obtained 2,6-DHN solution was analyzed under the following conditions.
(比較例1)フィルター通液なし
クラス1000のクリーンブース内にて、1000mL容量の四つ口フラスコ(底抜き型)に、有機純度99.3%の2,6−DHNをPGMEに溶解させた溶液(濃度2.5質量%)を500g仕込み、続いて釜内部の空気を減圧除去した後、窒素ガスを導入して大気圧まで戻し、窒素ガスを毎分100mLで通気下、攪拌しながら30℃まで加熱した。底抜きバルブから2,6−DHN溶液を抜き出し、フッ素樹脂製の耐圧チューブを経由してダイヤフラムポンプで毎分100mLの流量でフッ素樹脂製容器に回収した。回収した2,6−DHN溶液を下記条件にて分析した。(Comparative Example 1) No filter passage In a Class 1000 clean booth, 2,6-DHN having an organic purity of 99.3% was dissolved in PGME in a 1000 mL four-necked flask (bottomed mold). After charging 500 g of a solution (concentration 2.5% by mass), the air inside the kettle was removed under reduced pressure, nitrogen gas was introduced and returned to atmospheric pressure, and nitrogen gas was aerated at 100 mL per minute with stirring and 30 Heated to ° C. The 2,6-DHN solution was extracted from the bottom extraction valve and collected in a fluororesin container at a flow rate of 100 mL / min with a diaphragm pump via a fluororesin pressure tube. The collected 2,6-DHN solution was analyzed under the following conditions.
(実施例12)
2,6−DHNに変わり、純度99.2%の4,4−ビフェノールを使用した以外は、実施例1と同様に通液し、得られた精製溶液を下記条件にて分析した。(Example 12)
Instead of 2,6-DHN, except that 4,4-biphenol having a purity of 99.2% was used, liquid was passed in the same manner as in Example 1, and the obtained purified solution was analyzed under the following conditions.
(実施例13)
2,6−DHNに変わり、純度99.1%のレゾルシノール(1,3−ベンゼンジオール)を使用した以外は、実施例1と同様に通液し、得られた溶液を下記条件にて分析した。(Example 13)
Instead of 2,6-DHN, except that resorcinol (1,3-benzenediol) having a purity of 99.1% was used, liquid was passed in the same manner as in Example 1, and the obtained solution was analyzed under the following conditions. .
(実施例14)
2,6−DHNに変わり、純度98.7%の9,10−ジヒドロキシアントラセンを使用した以外は、実施例1と同様に通液し、得られた溶液を下記条件にて分析した。(Example 14)
Instead of 2,6-DHN, 9,10-dihydroxyanthracene having a purity of 98.7% was used, and the solution was passed in the same manner as in Example 1, and the obtained solution was analyzed under the following conditions.
(実施例15)
2,6−DHNに変わり、純度98.8%の1−ヒドロキシピレンを使用した以外は、実施例1と同様に通液し、得られた溶液を下記条件にて分析した。(Example 15)
The solution was passed in the same manner as in Example 1 except that 1-hydroxypyrene having a purity of 98.8% was used instead of 2,6-DHN, and the resulting solution was analyzed under the following conditions.
実施例1〜11及び比較例1において得られた2,6−DHNのPGME溶液、並びに精製前の2,6−DHNのPGME溶液(濃度2.5質量%)について、各種金属含有量及び有機純度を測定した。また、実施例1〜5においてはフィルターと同一材質からなる100μm厚のシート試験片(2cm×5cm)を用意し、当該シート試験片と精製前2,6−DHNのPGME溶液(濃度2.5質量%)との接触角測定を行った。測定結果を表1に示す。
さらに、実施例12〜15において得られた精製前後の各種ヒドロキシ置換化合物のPGME溶液について、各種金属含有量及び有機純度を測定した。また、フィルターと同一材質からなる100μm厚のシート試験片(2cm×5cm)を用意し、当該シート試験片と精製前の各種ヒドロキシ置換化合物のPGME溶液(濃度2.5質量%)との接触角測定を行った。測定結果を表2に示す。
なお、いずれの例においても、調製された溶液をフィルターに通液する直前を「精製前」として、その時点の溶液を上記測定に供することとした。
各測定については、次の装置及び測定条件にて行った。About the PGME solution of 2,6-DHN obtained in Examples 1 to 11 and Comparative Example 1, and the PGME solution of 2,6-DHN (concentration 2.5 mass%) before purification, various metal contents and organic Purity was measured. In Examples 1 to 5, a 100 μm-thick sheet test piece (2 cm × 5 cm) made of the same material as the filter was prepared, and the sheet test piece and a PGME solution (concentration 2.5) before purification were used. The contact angle with (mass%) was measured. The measurement results are shown in Table 1.
Furthermore, various metal contents and organic purity were measured about the PGME solution of the various hydroxy substituted compounds before and after purification obtained in Examples 12-15. In addition, a 100 μm-thick sheet test piece (2 cm × 5 cm) made of the same material as the filter is prepared, and the contact angle between the sheet test piece and a PGME solution (concentration: 2.5 mass%) of various hydroxy-substituted compounds before purification. Measurements were made. The measurement results are shown in Table 2.
In any of the examples, the time immediately before the prepared solution was passed through the filter was defined as “before purification”, and the solution at that time was subjected to the above measurement.
Each measurement was performed with the following apparatus and measurement conditions.
[各種金属含有量測定]
ICP−MSを用いて以下の測定条件にて2,6−DHNの各種金属含有量を測定した。
装置:ELAN DRCII(パーキンエルマー製)
温度:25℃
環境:クラス100クリーンルーム[Measurement of various metal contents]
Various metal contents of 2,6-DHN were measured under the following measurement conditions using ICP-MS.
Device: ELAN DRCII (manufactured by PerkinElmer)
Temperature: 25 ° C
Environment: Class 100 clean room
[有機純度測定]
高速液体クロマトグラフィーを用いて以下の測定条件にて2,6−DHNの有機純度を測定した。
装置:GL−7400型(日立製)
カラム:X−BRIDE C18
溶離液:アセトニトリル/水
温度:40℃[Organic purity measurement]
The organic purity of 2,6-DHN was measured using high performance liquid chromatography under the following measurement conditions.
Device: GL-7400 (Hitachi)
Column: X-BRIDE C18
Eluent: Acetonitrile / water Temperature: 40 ° C
[接触角測定]
接触角計を用いて以下の測定条件にて2,6−DHNおよび各ヒドロキシ置換化合物のPGME溶液と各シートとの接触角を測定した。
装置:協和界面化学(株)製CA−Sミクロ2型
測定手法:静滴法
雰囲気:空気中
測定環境:23℃/50%RH[Contact angle measurement]
The contact angle between the PGME solution of 2,6-DHN and each hydroxy-substituted compound and each sheet was measured using a contact angle meter under the following measurement conditions.
Apparatus: CA-S micro type 2 manufactured by Kyowa Interface Chemical Co., Ltd. Measurement method: Still-drop method Atmosphere: In air Measurement environment: 23 ° C./50% RH
本出願は、2015年9月4日出願の日本国特許出願(特願2015−174635号)に基づくものであり、その内容はここに参照として取り込まれる。 This application is based on a Japanese patent application (Japanese Patent Application No. 2015-174635) filed on Sep. 4, 2015, the contents of which are incorporated herein by reference.
本発明により、ヒドロキシ置換芳香族化合物を工業的に有利に精製することができ、金属含有量の低減された金属含有量の低減されたヒドロキシ置換芳香族化合物とすることができる。 According to the present invention, a hydroxy-substituted aromatic compound can be industrially advantageously purified, and a hydroxy-substituted aromatic compound having a reduced metal content and a reduced metal content can be obtained.
Claims (13)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2015174635 | 2015-09-04 | ||
JP2015174635 | 2015-09-04 | ||
PCT/JP2016/075774 WO2017038968A1 (en) | 2015-09-04 | 2016-09-02 | Compound purification method |
Publications (2)
Publication Number | Publication Date |
---|---|
JPWO2017038968A1 true JPWO2017038968A1 (en) | 2018-06-21 |
JP7306790B2 JP7306790B2 (en) | 2023-07-11 |
Family
ID=58188894
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2017538124A Active JP7306790B2 (en) | 2015-09-04 | 2016-09-02 | Compound purification method |
Country Status (4)
Country | Link |
---|---|
JP (1) | JP7306790B2 (en) |
CN (1) | CN108026011A (en) |
TW (1) | TW201718451A (en) |
WO (1) | WO2017038968A1 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP7067919B2 (en) * | 2017-12-26 | 2022-05-16 | 信越化学工業株式会社 | Purification method of dihydroxynaphthalene |
Citations (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5643228A (en) * | 1979-09-19 | 1981-04-21 | Mitsui Toatsu Chem Inc | Prevention of color development of aromatic compound having hydroxyl group |
JPH04235139A (en) * | 1990-05-29 | 1992-08-24 | Bromine Compounds Ltd | Process for preparing pure 4,4'-dihydroxybiphenyl |
JPH09208518A (en) * | 1996-02-05 | 1997-08-12 | Mitsubishi Gas Chem Co Inc | Production of high-purity naphthalenedicarboxylic acid |
JPH10212255A (en) * | 1997-01-30 | 1998-08-11 | Honshu Chem Ind Co Ltd | Production of crude 2,6-dialkylphenol |
JPH11512713A (en) * | 1995-09-28 | 1999-11-02 | クラリアント・インターナショナル・リミテッド | 4,4 '-[1- [4- [1- (4-hydroxyphenyl) -1-methylethyl] phenyl] ethylidene] bisphenol containing metal ions at low concentration and photoresist composition obtained therefrom |
JP2001114717A (en) * | 1999-10-19 | 2001-04-24 | Sumitomo Chem Co Ltd | Production of phenolic compound reduced with metal content |
JP2005023022A (en) * | 2003-07-03 | 2005-01-27 | Honshu Chem Ind Co Ltd | Method for producing high-purity 1,1-bis(4-hydroxyphenyl)cyclohexanes |
WO2006003810A1 (en) * | 2004-07-01 | 2006-01-12 | Tokyo Ohka Kogyo Co., Ltd. | Positive-working resist composition and method for resist pattern formation |
JP2008535878A (en) * | 2005-04-14 | 2008-09-04 | コグニス・アイピー・マネージメント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | Method for producing cardanol (I) |
JP2010107790A (en) * | 2008-10-31 | 2010-05-13 | Jsr Corp | Composition for forming resist lower layer film, and pattern forming method |
JP2011038062A (en) * | 2008-08-28 | 2011-02-24 | Sumitomo Chemical Co Ltd | Resin composition, gate insulating layer, and organic thin film transistor |
JP2011042583A (en) * | 2009-08-19 | 2011-03-03 | Kawasaki Kasei Chem Ltd | Method for producing aqueous solution of naphthohydroquinone compound and radical-trapping agent aqueous solution |
JP2011506553A (en) * | 2007-12-19 | 2011-03-03 | ロデイア・オペラシヨン | Method for preparing purified pyrocatechol |
JP2012190000A (en) * | 2011-02-25 | 2012-10-04 | Shin Etsu Chem Co Ltd | Positive resist material and patterning method using the same |
JP2012224793A (en) * | 2011-04-21 | 2012-11-15 | Maruzen Petrochem Co Ltd | Method for producing copolymer for semiconductor lithography containing reduced amount of metal impurities, and method for purifying polymerization initiator for production of the copolymer |
WO2012176767A1 (en) * | 2011-06-24 | 2012-12-27 | 日産化学工業株式会社 | Resist underlayer film forming composition containing polyhydroxybenzene novolac resin |
JP2014006403A (en) * | 2012-06-25 | 2014-01-16 | Shin Etsu Chem Co Ltd | Positive resist material and pattern forming method |
WO2014024836A1 (en) * | 2012-08-10 | 2014-02-13 | 日産化学工業株式会社 | Composition for forming resist underlayer film |
JP2014106263A (en) * | 2012-11-26 | 2014-06-09 | Shin Etsu Chem Co Ltd | Resist underlay film material and pattern forming method |
WO2014199662A1 (en) * | 2013-06-14 | 2014-12-18 | Dic株式会社 | Compound containing phenolic hydroxyl group, phenolic resin, curable composition, cured product thereof, semiconductor sealing material, and printed circuit board |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4235139B2 (en) | 2004-03-31 | 2009-03-11 | 株式会社間組 | Corrosion-resistant lining construction method |
JP5643228B2 (en) | 2009-12-25 | 2014-12-17 | 日本発條株式会社 | Connecting terminal |
CN103145531B (en) * | 2013-03-04 | 2014-08-20 | 丹东深兰化工有限公司 | Purifying and refining method of 1,5-dihydroxynaphthalene |
-
2016
- 2016-09-02 CN CN201680051083.4A patent/CN108026011A/en active Pending
- 2016-09-02 JP JP2017538124A patent/JP7306790B2/en active Active
- 2016-09-02 WO PCT/JP2016/075774 patent/WO2017038968A1/en active Application Filing
- 2016-09-02 TW TW105128482A patent/TW201718451A/en unknown
Patent Citations (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5643228A (en) * | 1979-09-19 | 1981-04-21 | Mitsui Toatsu Chem Inc | Prevention of color development of aromatic compound having hydroxyl group |
JPH04235139A (en) * | 1990-05-29 | 1992-08-24 | Bromine Compounds Ltd | Process for preparing pure 4,4'-dihydroxybiphenyl |
JPH11512713A (en) * | 1995-09-28 | 1999-11-02 | クラリアント・インターナショナル・リミテッド | 4,4 '-[1- [4- [1- (4-hydroxyphenyl) -1-methylethyl] phenyl] ethylidene] bisphenol containing metal ions at low concentration and photoresist composition obtained therefrom |
JPH09208518A (en) * | 1996-02-05 | 1997-08-12 | Mitsubishi Gas Chem Co Inc | Production of high-purity naphthalenedicarboxylic acid |
JPH10212255A (en) * | 1997-01-30 | 1998-08-11 | Honshu Chem Ind Co Ltd | Production of crude 2,6-dialkylphenol |
JP2001114717A (en) * | 1999-10-19 | 2001-04-24 | Sumitomo Chem Co Ltd | Production of phenolic compound reduced with metal content |
JP2005023022A (en) * | 2003-07-03 | 2005-01-27 | Honshu Chem Ind Co Ltd | Method for producing high-purity 1,1-bis(4-hydroxyphenyl)cyclohexanes |
WO2006003810A1 (en) * | 2004-07-01 | 2006-01-12 | Tokyo Ohka Kogyo Co., Ltd. | Positive-working resist composition and method for resist pattern formation |
JP2008535878A (en) * | 2005-04-14 | 2008-09-04 | コグニス・アイピー・マネージメント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | Method for producing cardanol (I) |
JP2011506553A (en) * | 2007-12-19 | 2011-03-03 | ロデイア・オペラシヨン | Method for preparing purified pyrocatechol |
JP2011038062A (en) * | 2008-08-28 | 2011-02-24 | Sumitomo Chemical Co Ltd | Resin composition, gate insulating layer, and organic thin film transistor |
JP2010107790A (en) * | 2008-10-31 | 2010-05-13 | Jsr Corp | Composition for forming resist lower layer film, and pattern forming method |
JP2011042583A (en) * | 2009-08-19 | 2011-03-03 | Kawasaki Kasei Chem Ltd | Method for producing aqueous solution of naphthohydroquinone compound and radical-trapping agent aqueous solution |
JP2012190000A (en) * | 2011-02-25 | 2012-10-04 | Shin Etsu Chem Co Ltd | Positive resist material and patterning method using the same |
JP2012224793A (en) * | 2011-04-21 | 2012-11-15 | Maruzen Petrochem Co Ltd | Method for producing copolymer for semiconductor lithography containing reduced amount of metal impurities, and method for purifying polymerization initiator for production of the copolymer |
WO2012176767A1 (en) * | 2011-06-24 | 2012-12-27 | 日産化学工業株式会社 | Resist underlayer film forming composition containing polyhydroxybenzene novolac resin |
JP2014006403A (en) * | 2012-06-25 | 2014-01-16 | Shin Etsu Chem Co Ltd | Positive resist material and pattern forming method |
WO2014024836A1 (en) * | 2012-08-10 | 2014-02-13 | 日産化学工業株式会社 | Composition for forming resist underlayer film |
JP2014106263A (en) * | 2012-11-26 | 2014-06-09 | Shin Etsu Chem Co Ltd | Resist underlay film material and pattern forming method |
WO2014199662A1 (en) * | 2013-06-14 | 2014-12-18 | Dic株式会社 | Compound containing phenolic hydroxyl group, phenolic resin, curable composition, cured product thereof, semiconductor sealing material, and printed circuit board |
Also Published As
Publication number | Publication date |
---|---|
TW201718451A (en) | 2017-06-01 |
WO2017038968A1 (en) | 2017-03-09 |
JP7306790B2 (en) | 2023-07-11 |
CN108026011A (en) | 2018-05-11 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2022184850A (en) | Purification method of compound or resin, and production method of composition | |
KR101381494B1 (en) | Purification process of fluorine-based solvent-containing solution | |
WO2006073173A1 (en) | Porous cured epoxy resin | |
WO2009049943A1 (en) | Removal of polar organic compounds and extraneous metals from organosilanes | |
WO2018061485A1 (en) | Liquid medicine, liquid medicine accommodation body, method for manufacturing liquid medicine, and method for manufacturing liquid medicine accommodation body | |
CN103601624B (en) | A kind of preparation method of acetone | |
IL263895B2 (en) | Hollow fiber membrane module and production method therefor, and epoxy resin used in hollow fiber membrane and production method | |
JP7306790B2 (en) | Compound purification method | |
JP6931198B2 (en) | Compound purification method | |
JP2020163372A (en) | Metal adsorbent for removal of metal impurities in epoxy resin and method for removing metal | |
JP2010234344A (en) | Hollow fiber membrane module and method of manufacturing the same | |
KR20190078538A (en) | Method for purifying dihydroxynaphthalene | |
JP2007056089A (en) | Method for producing purified epoxy resin | |
JP7233164B2 (en) | Method for producing hydroxy-substituted aromatic compound | |
JP6447628B2 (en) | Method for recovering anionic fluorine-containing emulsifier | |
JP2001011001A (en) | Metal removal from phenolic compound | |
JP6602301B2 (en) | Method for separating and recovering alkylene glycol monoalkyl ether, method for recycling resist composition processing waste liquid, and method for recycling resist composition processing liquid | |
CN114573425B (en) | Purification method and application of 1, 1-tri (4-hydroxyphenyl) compound | |
CN102500247A (en) | Modified cellulose acetate ultrafiltration membrane preparation method | |
EP3673975B1 (en) | Gas separation method and gas separation membrane | |
JP2004268510A (en) | Solution film making method | |
KR20080092379A (en) | Process for the treatment of an aqueous mixture comprising a dipolar aprotic compound | |
JP2002338584A (en) | Method for separation and purification of biphenyldiphosphinic acid | |
CN110559886A (en) | PIM-1/Pebax composite pervaporation membrane and preparation method and application thereof | |
WO2023022213A1 (en) | Method for producing everolimus |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20180117 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20190702 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20200413 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20200609 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20200811 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20201124 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20210118 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20210322 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20210524 |
|
C60 | Trial request (containing other claim documents, opposition documents) |
Free format text: JAPANESE INTERMEDIATE CODE: C60 Effective date: 20210524 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20210601 |
|
C21 | Notice of transfer of a case for reconsideration by examiners before appeal proceedings |
Free format text: JAPANESE INTERMEDIATE CODE: C21 Effective date: 20210602 |
|
A912 | Re-examination (zenchi) completed and case transferred to appeal board |
Free format text: JAPANESE INTERMEDIATE CODE: A912 Effective date: 20211015 |
|
C211 | Notice of termination of reconsideration by examiners before appeal proceedings |
Free format text: JAPANESE INTERMEDIATE CODE: C211 Effective date: 20211019 |
|
C22 | Notice of designation (change) of administrative judge |
Free format text: JAPANESE INTERMEDIATE CODE: C22 Effective date: 20220726 |
|
C22 | Notice of designation (change) of administrative judge |
Free format text: JAPANESE INTERMEDIATE CODE: C22 Effective date: 20230201 |
|
C13 | Notice of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: C13 Effective date: 20230221 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20230421 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20230629 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 7306790 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |